| Identification | Back Directory | [Name]
8-pCPT-2-O-Me-cAMP-AM | [CAS]
1152197-23-3 | [Synonyms]
8-pCPT-2-O-Me-cAMP-AM
8 pCPT 2 O Me cAMP AM,8pCPT2OMecAMPAM
8-(4-Chlorophenylthio)-2'-O-methyladenosine 3',5'-(acetyloxy)methyl)-cyclic monophosphate
Adenosine, 8-[(4-chlorophenyl)thio]-2'-O-methyl-, cyclic 3',5'-[(acetyloxy)methyl phosphate] | [Molecular Formula]
C20 H21 Cl N5 O8 P S | [MDL Number]
MFCD26792583 | [MOL File]
1152197-23-3.mol | [Molecular Weight]
557.9 |
| Chemical Properties | Back Directory | [Boiling point ]
757.2±70.0 °C(Predicted) | [density ]
1.80±0.1 g/cm3(Predicted) | [storage temp. ]
-20°C | [solubility ]
Soluble in DMSO (up to 50 mg/ml). | [form ]
solid | [pka]
2.88±0.10(Predicted) | [color ]
Colorless to light yellow | [Stability:]
Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 1 month. | [InChIKey]
FZMWUFYPEVDWPA-SILPBKOMSA-N | [SMILES]
NC1=NC=NC2=C1N=C(N2[C@H](O[C@H](CO3)[C@H]4OP3(OCOC(C)=O)=O)[C@@H]4OC)SC5=CC=C(C=C5)Cl |
| Hazard Information | Back Directory | [Description]
8-pCPT-2-O-Me-cAMP-AM (1152197-23-3) is a potent, cell-permeable Epac (exchange protein directly activated by cAMP) activator.1?Induces RAP1 activation and insulin secretion in pancreatic beta cell lines.2-5?Induces vascular relaxation in rat mesenteric artery.6?The acetoxymethyl ester confers increased cell-permeability and is cleaved by endogenous esterases to yield the active compound, 8-pCPT-2′-O-Me-cAMP. Addition to cell cultures should be done in serum-free media as esterases in serum will cleave the acetoxymethyl ester and reduce cell permeability. | [Uses]
8-pCPT-2-O-Me-cAMP-AM (cas# 1152197-23-3) is a useful research chemical.8-pCPT-2-O-Me-cAMP-AM was used in the study to discover potential insulin secretagogue properties of an acetoxymethyl that activates guanine nucleotide exchange factors. | [in vivo]
8-pCPT-2'-O-Me-cAMP-AM (intrarenal injection; ) activates renal Rap1 and likely is caused by activation of Epac in the tubular epithelium[1].
8-pCPT-2'-O-Me-cAMP-AM preserves renal function by Epac activation and reduces tubular epithelial-cell stress during ischemia[1]. | Animal Model: | IR injuried mouse model[1] | | Dosage: | 1.45 mM | | Administration: | Intrarenal injection; mice were sacrificed at 24, 48, or 72 hours after ischemia | | Result: | Protected renal injury during ischemia.
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| [storage]
Store at -20°C | [References]
1) Vliem?et al. (2008),?8-pCPT-2′-O-Me-cAMP-AM: an improved Epac-selective cAMP analogue; Chem. Biochem.,?9?2052
2) Chepurny?et al. (2009),?Enhanced Rap1 activation and insulin secretagogue properties of an acetoxymethyl ester of an Epac-selective cyclic AMP analog in rat INS-1 cells: studies with 8-pCPT-2′-O-Me-cAMP-AM; J. Biol. Chem.,?284?10728
3) Kelley?et al. (2009),?Glucose-dependent potentiation of mouse islet insulin secretion by Epac activator 8-pCPT-2′-O-Me-cAMP-AM; Islets,?1?260
4) Chepurny?et al. (2010),?PKA-dependent potentiation of glucose-stimulated insulin secretion by Epac activator 8-pCPT-2′-O-Me-cAMP-AM in human islets of Langerhans; Am. J. Physiol. Endocrinol. Metab.,?298?E622
5) Dzhura?et al. (2011),?Phospholipase C-ε links EPAC2 activation to the potentiation of glucose stimulated insulin secretion from mouse islets of Langerhans; Islets,?3?121
6) Roberts?et al. (2013),?Exchange protein activated by cAMP (Epac) induces vascular relaxation by activating Ca2+-sensitive K+ channels in rat mesenteric artery; J. Physiol.,?591?5107 |
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